2-Amino-5-butyl-4-methyl-1,3-thia­zol-3-ium nitrate

The title compound, C₈H₁₅N₃O₃S, shows bond lengths and angles that are typical and are in accordance with expected values. The structure comprises a substituted thia­zolium ring that is connected to a nitrate ion via N—H...O hydrogen-bonding interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.131
• Data-to-parameter ratio = 18.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(I)

Crystal data

C8H15N3O3S	Z = 2
Mr = 233.29	F(000) = 248
Triclinic, P1	Dx = 1.338 Mg m^−3 Dm = 1.319 Mg m^−3 Dm measured by flotation
a = 7.486 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.918 (2) Å	Cell parameters from 4395 reflections
c = 9.240 (2) Å	θ = 3.6–28.0°
α = 76.26 (3)°	µ = 0.27 mm^−1
β = 87.15 (3)°	T = 293 K
γ = 75.08 (3)°	Irregular, colourless
V = 579.0 (2) Å^3	0.2 × 0.15 × 0.1 mm

Data collection

Xcalibur diffractometer	2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 28.0°, θmin = 3.6°
Detector resolution: 1024 × 1024 with blocks 2 × 2 pixels mm^-1	h = −10→8
ω scans	k = −12→11
4395 measured reflections	l = −12→11
2712 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0762P)^2] where P = (Fo^2 + 2Fc^2)/3
2712 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.21746 (7)	0.40896 (6)	0.22923 (6)	0.02014 (17)
C5	0.0041 (3)	0.5388 (2)	0.2564 (2)	0.0177 (4)
C4	−0.1368 (3)	0.4953 (2)	0.2082 (2)	0.0186 (4)
N3	−0.0763 (2)	0.3590 (2)	0.15014 (19)	0.0175 (4)
H3A	−0.162 (3)	0.316 (3)	0.116 (3)	0.021*
C2	0.1065 (3)	0.2972 (2)	0.1535 (2)	0.0173 (4)
N6	0.1918 (3)	0.1695 (2)	0.1041 (2)	0.0206 (4)
H6A	0.303 (4)	0.133 (3)	0.113 (3)	0.025*
H6B	0.123 (3)	0.115 (3)	0.071 (3)	0.025*
C7	−0.3394 (3)	0.5703 (2)	0.2126 (3)	0.0217 (4)
H7A	−0.3588	0.6616	0.2548	0.033*
H7B	−0.3995	0.4944	0.2725	0.033*
H7C	−0.3899	0.6031	0.1132	0.033*
C8	−0.0073 (3)	0.6769 (2)	0.3275 (3)	0.0218 (4)
H8A	−0.0738	0.6592	0.4202	0.026*
H8B	−0.0793	0.7734	0.2623	0.026*
C9	0.1783 (3)	0.7043 (2)	0.3600 (2)	0.0210 (4)
H9A	0.2535	0.6076	0.4227	0.025*
H9B	0.2432	0.7288	0.2674	0.025*
C10	0.1509 (3)	0.8412 (3)	0.4381 (2)	0.0242 (5)
H10A	0.0769	0.9375	0.3740	0.029*
H10B	0.0824	0.8172	0.5288	0.029*
C11	0.3315 (4)	0.8729 (3)	0.4772 (3)	0.0339 (6)
H11A	0.3046	0.9600	0.5258	0.051*
H11B	0.3989	0.8995	0.3878	0.051*
H11C	0.4044	0.7791	0.5427	0.051*
N12	0.6761 (2)	0.1062 (2)	0.1077 (2)	0.0201 (4)
O13	0.5809 (2)	0.00502 (18)	0.14171 (19)	0.0284 (4)
O14	0.8421 (2)	0.06598 (19)	0.0696 (2)	0.0321 (4)
O15	0.6067 (2)	0.25091 (18)	0.11105 (19)	0.0277 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0147 (3)	0.0195 (3)	0.0288 (3)	−0.00064 (19)	−0.00108 (19)	−0.0143 (2)
C5	0.0149 (9)	0.0163 (9)	0.0215 (10)	−0.0001 (7)	0.0018 (7)	−0.0079 (8)
C4	0.0182 (9)	0.0156 (9)	0.0214 (10)	0.0003 (8)	0.0020 (8)	−0.0083 (8)
N3	0.0171 (8)	0.0154 (8)	0.0224 (9)	−0.0027 (7)	0.0005 (7)	−0.0107 (7)
C2	0.0173 (9)	0.0143 (9)	0.0199 (10)	−0.0014 (7)	0.0007 (7)	−0.0060 (8)
N6	0.0153 (8)	0.0190 (9)	0.0308 (10)	−0.0020 (7)	0.0009 (7)	−0.0146 (8)
C7	0.0156 (10)	0.0188 (10)	0.0299 (12)	0.0004 (8)	−0.0003 (8)	−0.0092 (9)
C8	0.0190 (10)	0.0186 (10)	0.0302 (12)	−0.0010 (8)	0.0006 (8)	−0.0143 (9)
C9	0.0209 (10)	0.0199 (10)	0.0247 (11)	−0.0039 (8)	0.0009 (8)	−0.0113 (8)
C10	0.0306 (12)	0.0204 (10)	0.0235 (11)	−0.0060 (9)	0.0029 (9)	−0.0098 (9)
C11	0.0415 (14)	0.0310 (13)	0.0358 (14)	−0.0151 (11)	−0.0049 (11)	−0.0128 (11)
N12	0.0180 (8)	0.0179 (8)	0.0263 (10)	−0.0008 (7)	−0.0010 (7)	−0.0127 (7)
O13	0.0196 (8)	0.0222 (8)	0.0473 (10)	−0.0080 (6)	0.0045 (7)	−0.0136 (7)
O14	0.0166 (7)	0.0332 (9)	0.0554 (11)	−0.0067 (7)	0.0100 (7)	−0.0288 (8)
O15	0.0241 (8)	0.0177 (7)	0.0429 (10)	0.0023 (6)	−0.0045 (7)	−0.0174 (7)

Geometric parameters (Å, º)

S1—C2	1.729 (2)	C8—H8A	0.9700
S1—C5	1.761 (2)	C8—H8B	0.9700
C5—C4	1.342 (3)	C9—C10	1.526 (3)
C5—C8	1.509 (3)	C9—H9A	0.9700
C4—N3	1.404 (2)	C9—H9B	0.9700
C4—C7	1.494 (3)	C10—C11	1.527 (3)
N3—C2	1.336 (3)	C10—H10A	0.9700
N3—H3A	0.93 (2)	C10—H10B	0.9700
C2—N6	1.325 (2)	C11—H11A	0.9600
N6—H6A	0.81 (3)	C11—H11B	0.9600
N6—H6B	0.90 (3)	C11—H11C	0.9600
C7—H7A	0.9600	N12—O14	1.258 (2)
C7—H7B	0.9600	N12—O13	1.263 (2)
C7—H7C	0.9600	N12—O15	1.268 (2)
C8—C9	1.527 (3)
C2—S1—C5	90.9 (1)	C5—C8—H8B	108.5
C4—C5—C8	127.3 (2)	C9—C8—H8B	108.5
C4—C5—S1	110.94 (14)	H8A—C8—H8B	107.5
C8—C5—S1	121.7 (1)	C10—C9—C8	110.87 (17)
C5—C4—N3	112.26 (17)	C10—C9—H9A	109.5
C5—C4—C7	128.51 (18)	C8—C9—H9A	109.5
N3—C4—C7	119.2 (2)	C10—C9—H9B	109.5
C2—N3—C4	115.45 (17)	C8—C9—H9B	109.5
C2—N3—H3A	124.5 (15)	H9A—C9—H9B	108.1
C4—N3—H3A	120.0 (15)	C11—C10—C9	113.70 (19)
N6—C2—N3	125.07 (18)	C11—C10—H10A	108.8
N6—C2—S1	124.49 (16)	C9—C10—H10A	108.8
N3—C2—S1	110.43 (14)	C11—C10—H10B	108.8
C2—N6—H6A	121.5 (18)	C9—C10—H10B	108.8
C2—N6—H6B	118.6 (15)	H10A—C10—H10B	107.7
H6A—N6—H6B	119 (2)	C10—C11—H11A	109.5
C4—C7—H7A	109.5	C10—C11—H11B	109.5
C4—C7—H7B	109.5	H11A—C11—H11B	109.5
H7A—C7—H7B	109.5	C10—C11—H11C	109.5
C4—C7—H7C	109.5	H11A—C11—H11C	109.5
H7A—C7—H7C	109.5	H11B—C11—H11C	109.5
H7B—C7—H7C	109.5	O14—N12—O13	120.81 (17)
C5—C8—C9	115.28 (17)	O14—N12—O15	118.39 (18)
C5—C8—H8A	108.5	O13—N12—O15	120.80 (17)
C9—C8—H8A	108.5
C2—S1—C5—C4	−0.44 (17)	C4—N3—C2—N6	−179.80 (19)
C2—S1—C5—C8	178.71 (18)	C4—N3—C2—S1	−0.7 (2)
C8—C5—C4—N3	−178.94 (19)	C5—S1—C2—N6	179.74 (19)
S1—C5—C4—N3	0.1 (2)	C5—S1—C2—N3	0.63 (16)
C8—C5—C4—C7	−0.2 (4)	C4—C5—C8—C9	−175.5 (2)
S1—C5—C4—C7	178.85 (18)	S1—C5—C8—C9	5.5 (3)
C5—C4—N3—C2	0.4 (3)	C5—C8—C9—C10	−177.37 (18)
C7—C4—N3—C2	−178.48 (19)	C8—C9—C10—C11	178.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O13	0.81 (3)	2.10 (3)	2.901 (3)	171 (2)
N3—H3A···O14^i	0.92 (3)	2.36 (3)	3.090 (3)	135 (2)
N3—H3A···O15^i	0.92 (3)	1.97 (3)	2.849 (3)	157 (2)
N6—H6B···O14^i	0.90 (3)	2.25 (3)	3.045 (3)	146 (2)
N6—H6B···O14^ii	0.90 (3)	2.25 (3)	2.994 (3)	138 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z.